Great leaders know how to lead people through the most complex of paradoxes. That is one of the problems the world faces today – our leaders are facing ever complex paradoxes and no one knows how to lead us through them. For example, Presidents Obama and Bush wrestled with this paradox – balance the budget and don’t cut programs or raise taxes. A paradox is a situation that appears to hold two contradictory statements and each restricts or limits the other. Since paradoxes appear frequently in businesses and organizations today, leaders need to know how to guide themselves and their teams through the mazes that paradoxes present.

Okay, What is a Paradox Again? I remember hearing the term for the first time in high school when we read the book Catch-22 by Joseph Heller, who was a WWII bomber pilot. The term “Catch-22” has evolved over time to mean a “no win situation.” The book tells the challenging story of what it was like being a bomber pilot during World War II. Every time they flew there was a high risk of death. The expression grew out of this paradox - you could get out of flying if you were classified as “insane,” but if you asked for an insanity evaluation to get out of flying, you had to be sane. That was the “catch.” So, the “Catch-22” paradox is one where the system itself appears to prevent you from solving the problem. This is, really, the most complex type of paradox.

What are Some Common Leadership Paradoxes? As a leader, you are likely to bump into many common paradoxes. The first one I remember as a young banker was this one – I want to be liked by this businessperson but he doesn’t qualify for the loan he requests. Then, when I began leading people in my branches I remember this one – My best performer deserves a nice raise but my personnel budget is so tight I don’t have money available for raises.

Here are other common paradoxes leaders face:

1. I want to trust what my team does and I need to verify what they do.
2. I want to inspire my team with my charisma and be humble.
3. I want to use consensus and be decisive so the team has confidence in me.
4. I want to be liked as a friend by my team and keep my distance so I can provide constructive feedback.
5. I want to effectively manage my time and be flexible to listen to the needs of my team.
6. I want to directly communicate areas that need improvement with my team members and be diplomatic so as not to hurt their feelings.

How To Deal With Paradoxes. You start to deal with paradoxes by writing them down. Usually our brains put a “but” between the limiting or conflicting statements, as I did in my banker example. However, I recommend you challenge yourself to put the paradox into a statement that uses “and” instead. This is a subtle, but important distinction. Notice I did that in the prior section for each of the six common examples I gave you. When we work with our teams to solve the paradox by optimizing all the limiting conditions, we get the best results.

Once you have written the paradox this way, I suggest leaders engage appropriate team members in discussions about the paradox. The leader’s job is to think about and write questions that help teams solve the paradox. The goal is to arrive at solutions that satisfy both ends of the “and” or "but" statement. Unfortunately leaders don’t often prepare properly for these discussions and, as a result, develop strategies that only satisfy one half of the paradox.

Here are a few questions you could use to discuss my first example above:

• How do I show my team I trust them?
• What do I need to do to verify that what they are doing is what we want them to do?
• How can I verify in such a way that it shows them I trust them?

“Ah, but I was so much older then, I’m younger than that now.” (Bob Dylan, “My Back Pages”.) I remember when I first heard this line I wondered what Dylan meant. On the surface it seemed like a paradox – you can’t be older then and younger now. As I’ve thought about this line, though, I realize he may have had another lesson for us – when you are young you think you know everything and as you grow older you realize how little you know. And isn’t that the greatest leadership paradox of all?